Crooked Smile
by Cathy Gilmore
Summary: Set, beg S2. Luke and Lorelai have just gotten married but Rory has become rather bored of her perfect life until a certain bad boy comes to live with them. Things are about to get intersting. WARNING: QUITE MATURE.
1. Woes of A Good Girl and A Very Bad Boy

Disclaimer: if i owned the rights to the gilmore girls do you really think i'd be posting here? All rights belong to ASP. (I'm only gonna say this once!)

**Okay, this is the first chapter of my new story, it took a while but I finally think it's ready. My FAOF readers please don't worry, the next chapter will be up shortly, but I just wanted to see what people thought of this before I continue. Though I should warn you that this will be a bit more mature and Rory may seem a bit OOC at times but I will try to stay true to her character as much as possible.**

**Crooked smile**

**The Woes of a Good Girl**** and A Very Bad Boy**

Rory Gilmore was seventeen years old and lived a wonderful, blessed life; with a loving family, in a supportive, close nit community. She and her mother were freakishly linked; sometimes it felt as if she was more like her sister and best friend, but she could be just her mother when she really needed her to be. They had lived in Stars Hollow since Rory was a baby, just the two of them. Rory's father would check in with them every once and a while but she came to understand at a very young age that he would never be a staple in her life. Recently though, her mother had decided to add to the number of people living in the Gilmore house. Twelve months ago, after years of continuous flirting and of being an agonising tease, Lorelai had finally decided to through caution into the wind and began to date Stars Hollow's own surly diner man himself. She couldn't have been happier for her mother; they were perfect for each other; though many of the townsfolk placed bets on how long it would last. Three months ago, however, all bets were off when the two finally tied the knot. Luke was now her step – father. Her family was now complete. On top of that, she and her wonderful, caring boyfriend Dean had just had there one year anniversary, she had great friends, her school routine was down, her grades were great, as was everything else. Yep, everything was great. Great, except for one thing. She was so bored!

She knew it might have sounded ungrateful but there were only so many light and fluffy, like cotton candy days a person can take before they're physically sick. She needed some excitement. Nothing in her life was thrilling; she always played everything so safe, right down to the gut she was seeing, she was safe. It's not that she didn't care about Dean; she wouldn't have stayed with him so long if she didn't, right? At first everything had been great, he was just what she wanted; kind, polite, her mother liked him but now, every time she was with him it felt like there was something missing. She couldn't think why, Dean hadn't really changed, he was slightly more possessive but other than he was exactly the same. Exactly. Maybe that was the problem? Dean may not have changed but her wants and needs certainly had. That's why she'd done something bad –very bad. Well, for her, anyway.

She didn't know what had come over her, but she just couldn't help it. It was a Wednesday afternoon, about four weeks ago, and the bell had just ringed, signalling the start of the lunch break. She was just walking through the hall, when suddenly somebody grabbed her arm and pulled her into the girls' bathroom. Tristan.

"_What the hell do you think your doing?" she'd asked, appalled. He didn't answer; he just pushed her up against the door and forced his lips onto hers. She wanted to push him away and slap him across the face. She had a boyfriend, of which he was fully aware! A million thoughts were running around her head. She couldn't do this! She shouldn't do this! But as soon as he started nibbling on her bottom lip she lost control. Instead of pushing him away, she wrapped her arms around his neck and pulled him closer. All of a sudden they were heavily making out in the middle of the girls bathroom. After a while, he moved her across the room and propped her up next to the sink. They continued there for a time, and then his hand began to move up her leg. She didn't mind it at first; at least she knew for sure he was a bit more adventurous than Dean. But when he started to move up her skirt she pulled away, and then ran from the room without looking back._

She still couldn't believe what had happened. However, that was not all. A few days later it happened again. And then again and that's how it continued for a few weeks until the moron got himself shipped off to military school. She wasn't heartbroken over this as they both knew it wasn't the romance of the century, or even a romance at all but she was sure going to miss the distraction he gave her and the occasional thrill. Oh, God, when had she become this girl? The girl toying around with boys feelings, one of those girls she despised. It wasn't that she didn't care for Dean, she did, truly but lately it was more like caring for a friend than a boyfriend. She knew she should break up with him but everyday he told her he loved her and she just couldn't bring herself to crush him. That's why Tristan had been so convenient. He was no where near Stars Hollow, and they only got together during school hours so Dean had no reason to suspect anything. However, she had suspected that Tristan may have hoped it would blossom into something more but she always tried to make it clear that wasn't what she was looking for. She had that. She'd had enough of that.

She knew it was trivial but she wanted the toe curling romance she read about in books and saw in movies. Some people would say it doesn't exist, that it's all make believe, but she refused to believe it. She wouldn't rest until she found that passion in her life. But all that would have to wait. It was now eight on a Saturday morning and she could smell the pancakes Luke was making in the kitchen and decided it was time for breakfast. She opened her door and walked into to the kitchen, and saw Luke standing next to the stove and Lorelai reading the paper at the table. Lorelai looked up and smiled at her.

"Morning, sweets."

"Morning Mom, morning Luke." She smiled and then sat down next to her mother.

"Hey, Rory. Do you want some pancakes?"

"You know it!" she sat down at the kitchen table, after pouring herself a cup of coffee. "Umm, this is a good cup of coffee! It's so much more convenient having our favourite diner owner living with us, now!"

"Isn't it!" grinned her mother.

"It's nice to know I'm appreciated!" said Luke as he handed Rory her pancakes.

"Thanks, Luke. Hey, shouldn't you be at the diner right now?"

"Err, no, I got Caesar to open up today."

"Oh, why, are you two up to something?"

"No, Jess is coming today." Oh, right, Jess; Luke's wayward nephew. She never met him before. Or his mother. She got the impression that she and Luke weren't very close, especially when she hadn't turned up at the wedding. But she still had the nerve to dump her kid on him when things got a little tough for her. She phoned to ask him about it about a month ago. Luke and Lorelai had spent two weeks discussing Jess moving in with them and in the end they decided that they would try and help him onto the right path. There was plenty of space since they had built the extension onto the house just before Luke moved in and Luke was pretty much convinced that if Jess was left any longer in his mother's care he end up in prison or dead. However, they hadn't really asked Rory what she thought about it, she wouldn't have objected, but she couldn't help but remember a time when her mother checked with her about everything.

"What time does he get here?"

"Around ten. Do you two want to come and meet him at the bus stop with me, or do you just want to wait until later."

"Err, later. I promised Lane I'd meet up with her today." said Rory, but as Lorelai began to speak her phone went off, and she began rushing around the house trying to find her shoes. "Oh, there was some crisis at the inn, I'm gonna have to leave early. Sorry, I can't come with you babe."

"Oh, okay." And with that, and a kiss on the lips for Luke and one on the cheek for Rory she was the door. Leaving them alone.

Rory and Luke chatted for a little while longer as she finished her breakfast and then she ran to meet Lane. She really needed someone to vent to. Lane was the only person she had told about Tristan, she wasn't really approving but Rory knew that Lane would always be understanding. She met her at the gazebo, away from the prying ears of Mrs Kim.

"Do you think that I should tell Dean about Tristan?" Her friend looked at her incredulously.

"Are you INSANE! Come on Rory, you said that this "fling," for lack of a better word, was just that – "a fling." As in nothing serious! And you said Tristan was gone now, so what's the point of breaking Dean's heart? He's crazy about you Rory! Maybe if you tell him that you need some space he'll ease off and things will be good again!" Rory sighed.

"I just feel like there's something missing."

"Well, if things don't get better then you should break up with him so that you both have a chance of being happy with someone else." Lane gave her a sympathetic look and Rory nodded.

"You're right. You're absolutely right." Lane looked at her watch and sighed.

"I've gotta go, Mamma said I had to help her do inventory today. But hey do you wanna hang out tonight?"

"Oh, sorry I can't. Luke's nephew's coming to town today and we're all going to have dinner together to get him settled."

"Is it weird that you're going to have another guy living in your house? One that you've never met before, I might add."

"Ugh, I know. On top of everything else I have to deal with now I have put up yet another member of the male species. He's probably going to be some pimply stoner that probably doesn't know the difference between Hemmingway and a Hamburger!"

"Hemmingway is a dead writer, right?" asked Lane, smirking.

"FUNNY!" Lane laughed.

"I'll see you later." Rory waved goodbye to her friend and then got up to go for a walk around town, trying to figure out what she was going to say to Dean.

Luke meanwhile was sat at the bus stop waiting for his nephew to arrive. He still couldn't believe Lorelai had agreed to let Jess to come and live with them. She'd never met him and he hadn't seen him for ages. He was just getting used to being a married with one teenager to look out for, how would he cope with living with another one? He shook his head; it was too late to back out now. He and Lorelai had pent weeks talking everything through, and he knew that this would be best for him. Liz was finally trying to get her life together and he thought that was great, but she had already screwed up her son's life so far and he thought it was best for Jess to have some stability while Liz got her act together. He knew he probably should have got involved sooner but he and Liz weren't really on speaking terms for a good few years. But now he could try and help. Hopefully, with Loralai's help he could stop him from falling off the face of the earth. Or worse, like his father, wherever the hell he was. Luke was pulled out of is train of thought, as the bus pulled up in front of him. Several people got off, until finally he saw a mass of unruly hair descend the bus steps.

"Jess." He nodded.

"Luke." He scowled. Luke nodded again and then led him the way to their house. Jess followed, hauling his duffle bag over his shoulder as he walked. On the way, Jess couldn't believe his eyes. It was as though Willy Wonka had thrown up on the place. There were mothers and daughters dressed the same, and everywhere he looked someone was skipping. And on one street corner he could have sworn that there were teenagers sitting at a lemonade stand. What was wrong with these people? His mother had grown up here? Huh, maybe her smoking pot for the better part of her life wasn't the only reason she was such a basket case? When they got to the house he stopped outside for a moment to take it in, it looked relatively normal but looks can be deceiving.

"Okay," voiced Luke, when they finally got inside, "this is it. Your room is upstairs and then down the hall from mine and Lorelai's, just on the right. There's a bathroom upstairs next to your room and there's one next to the kitchen, across from Rory's room. Both her and Lorelai will be home later." Jess just nodded, dumbly. "So, is that all your stuff?" He asked, signalling to Jess' duffel bag.

"Yep."

"There's not much there."

"Yeah, well, Lizzie's sending the rest later."

"Right, right. So, do you want something to eat? I could see what we have in the fridge or you could come to the diner with me?"

"Diner?"

"Yeah, that's what I do. I own a diner; it was your Grandpa's old store-"

"Huh." Jess nodded, feigning interest.

"So, do want something to eat?" Jess shook his head.

"No, thanks. I think I'll just stay here and take a shower. Being on a bus for any extended period of time can make you itch."

"Sure. Oh, but now that I think about it, the shower upstairs isn't really working properly, there's no pressure coming through, so you'll have to use the one down here. The towels are in the closet next to mine and Lorelai's room, on the left."

"Okay, thanks." They stood in an awkward silence for a moment before Luke decided it was okay for him to leave.

"Well, I better get going to work. Rory should be back soon and Lorelai usually gets home at about six so we'll all have dinner together tonight and you can get to know them. So, I'll see you tonight."

"See, you tonight." And with that Luke turned to the door and left, leaving Jess alone in the house. He sighed and looked around the room. Well, it could be worse. He picked up his duffel bag and went upstairs to find his room. He went to the end of the corridor on the right and open the door, to what he assumed was his room. It was a decent size and rather plainly decorated with pale blue walls and several empty white shelves and cabinets. In the centre of the room there was a double bed with dark, stripy blue sheets that matched the curtains, which he assumed had been picked out especially for his arrival. He walked over to the bed and dumped his duffel bag on the bed, along with his jacket. He then moved over to the window and looked out at the town of Stars Hollow. The sun was shining brightly, birds were singing, children were laughing, running and skipping, some were even wearing the same clothes as their parents – it made him SICK! What was Liz thinking sending him here! He'd probably try to kill himself by the end of the week! She must have known that, she grew up here. Oh, boy, that explained a lot! He shook his head and headed for the shower; he was beginning to repeat himself in his own mind thanks to this place. He might feel better after a wash but he doubted it.

--

Rory walked back into the house, very depressed. She'd been walking around the town for over an hour, trying to figure out what to say to Dean. She really didn't want to hurt him but she didn't want to be with him anymore. She began to walk to her room and realised as her mom and Luke wouldn't be home yet, and as their shower was on the blink, now would be a good time to take one. She opened her bedroom door and began to peel off her clothes. As soon as she had unclasped her bra and thrown it onto her bed, the bathroom door behind her opened and she whipped around in shock. Stood there was perhaps the most gorgeous boy she had ever seen, dripping wet and completely naked apart from the stripy blue towel around his waste. He had sexy dark hair and olive skin, but she couldn't help but stare at his well toned chest. It wasn't until her eyes made it back up to his face that she realised he was also staring at her very naked chest!

"OH MY GOD!" she screamed, grabbing her bathrobe off the door and covering herself, as he stumbled back a little. "WHO THE HELL ARE YOU! AND WHAT ARE YOU DOING IN MY SHOWER!"

--

Jess had been in the shower for about twenty minutes when he decided that he had finally gotten rid of the grungy bus smell, and stepped out grabbing his towel from the railing. He wrapped it around his waste and unlocked the door. No sooner had he opened it, when he greeted by someone else's bare flesh. At first he saw nothing but her back but barely a second later, he was faced with a pair of creamy - white breasts. He seemed to be staring at them for ages before-

"OH MY GOD!" she screamed, as he stumbled back, holding his towel on his waist. "WHO THE HELL ARE YOU! AND WHAT ARE YOU DOING IN MY SHOWER!"

"I'm Jess, Luke's nephew. I got here about thirty minutes ago. Luke told me to use this shower, the one upstairs is broken." She sighed and closed her eyes nodding; oh yeah, now she remembered. She was about to apologise, when she realised they were both still half naked, and then quickly shut her bedroom door. DEAR LORD, 'HE' was going to be staying with them! She wasn't sure if it was better or worse, but one thing was for sure: she had enough boy troubles.

--

After she had slammed her bedroom door shut, he stood there for another few moments stunned. WOW, he never expected a meeting like that! He then realised he was dripping on the floor and was about to head upstairs but then decided it would be best if he took another shower. A cold shower. But on the bright side, Stars Hollow might not be that bad after all.

--

**A/N : HHMM, not quite the same innocent meeting it was originally but I hope you enjoyed it just the same. Please tell me what you think. Or if you hav any questions please PM me.**


	2. Late Night Musings

Disclaimer: I do not own Gilmore Girls. ( If I did I would have chained Milo to a chair and never let him leave.)

**It's heeeerrrreee! The second chapter is up! Finally!**

**Crooked Smile**

**Chapter 2 – Late Night Musings**

Dinner that evening had been excruciating; Rory had refused to look at him all night, and it was all he could do to stop his eyes from focusing on her chest. It was incredibly hard in fact, especially considering her mother and Luke just wanted to ask him questions all night and he had to do his best to avoid them also. Was his journey okay? Did he like his room? Was the colour okay? Did he like being here? Did he need anything? Toothbrush, school books, underwear, or a long rope for him to hang himself with? On and on and on, it was never ending! He'd been shipped off to a place that looked as if it was twinned with Oz, without notice or his consent; what did they expect, _cartwheels?!_ Rory locked herself in her room as soon as dinner finished. Lorelai tried to get her to stay and _chat_ but said she didn't feel well and went straight to bed. Taking inspiration from this, Jess pretended to be tired from the move and went to bed also.

Which is where he was now, lying wide awake in his bed, listening to the deafening silence. There were no police cars driving by, or any cars for that matter. There were no people shouting in the street, or through the thin walls of his apartment building. He felt as if he was the last man on earth, left alone after some sort of nuclear explosion had taken place. He normally didn't mind solitude, but without evening dull buzzing of another human voice, he was finding it difficult not to scream out loud. Jess sat up in his bed and looked at the clock; eleven. Unbelievable. If he was back in New York, he would probably just be heading out. This was partly the reason for why he was sent to Stars Hollow, in the first place. Well, not that Liz ever really noticed when he wasn't around. When she was listing her reasons for sending him to Stars Hollow, he figured it was more, lucky guess work, on her part.

He got out of his bed, walked over to the window and opened his curtains. It was pitch black. With so few street lights he felt as if he had been sucked into a vortex while he'd been sleeping. He ruffled his hair in frustration. He was dying for a smoke! He was really only a casual smoker – he really just did it when his friends were around, or to piss off his mom – but tonight he felt as if that he didn't have one he was going to put his head threw a wall. He was going to sneak one after dinner, but he thought Lorelai might come looking for him. He wouldn't have cared if Luke had caught him but Lorelai scared him. Nobody could be that friendly without being on some sort of medication. He turned looked out of the window again. From the dark shapes he could make out, he realised that the back door was below his window. He figured if he started smoking out of his window, there was a chance that either, Lorelai would smell it or some freak of neighbour would still be up and see it – they looked like the type of people that owned night vision equipment. But if he crept downstairs and out of the back door he could probably get away with it. Normally, he wouldn't have cared if he got caught smoking or not, but he was too tired to deal with a lecture tonight.

He pulled a pack out of his duffel bag and then proceeded to creep out of the door, and down the hallway. When he got to the top of the stairs he paused. Did any of the stairs squeak? He decided to chance it, and quickly rushed down them. As he moved towards the kitchen, he paused slightly outside of Rory's bedroom door. It was weird. He'd never really given a girl he barley knew so much thought before. He shook his head, and proceeded into the kitchen and then out the backdoor. How quaint, he thought. Nobody even bothers to lock the doors here. He sat down on the step, and lit his first cigarette. He then took a long glorious drag. It was like taking his first breath after holding it for twenty four hours. He then leaned back against the door and sighed, looking out towards the complete blackness of the night. What had he done to get himself sent here? He then smirked, beside himself, at this thought. The question wasn't 'what had he done'! It was what hadn't he done? Drinking, fighting, stealing and meaningless sex was just what made up the average Friday night to him. Some would call it attention seeking; a desperate plea for some kind of acknowledgment that he was actually alive, from a mother that was too stoned to tell what day of the week it was. But Jess he knew that this would be pointless. Liz never cared about what he did, where he went or who with, she was just glad that he was out of her sight. No, Jess merely acted out because it didn't matter that he did, and it was more entertaining to live his life dangerously that as a boy scout. His mother had only sent him because she was tired of the police showing up at her door, particularly when one of her crack head boyfriends was in the house; though she may have claimed otherwise. He thought about earlier in the day, when his life was just the same as it ever was, and then she tells him she was sending him to live in Hicks Ville with an uncle whom he hadn't seen since he was six.

_Flashback _

_It was nine o'clock in the morning, when he walked into his living room and found it completely covered in boxes. And his mother, sober for once, labeling them all. _

"_What the hell is all this?!"_

"_Moving boxes." His mother stated simply. He chuckled or rather snorted in mild disbelief._

"_So which one of your coke head boyfriends are we moving in this week? Or, wait, haven't you quite decided yet, but just want to get a jump start on the packing anyway?" Now under normal circumstances this would have resulted in a random object being flung at his head but this day Liz had kept her cool, and ignored it. _

"_We're not moving."_

"_Okay- so what's with-?"_

"We're_ not moving _you_ are!"_

"_WHAT! YOU'RE KICKING ME OUT! Now, I know your maternal instincts aren't all that slipshod, no matter how much pot you smoked while you were pregnant with me! Tossing your only child out onto the street is just a tad bit callous, even for you!" He couldn't even look at her. He stormed across the room into the kitchen, and then pulled a beer out of the fridge. Liz followed him; trying her very best to remain calm._

"_I'm not throwing you out onto the street. I'm sending you to Connecticut, to live with your uncle. I bought you a bus ticket, you leave in an hour. I want you to pack your duffel bag with the stuff you will need for the rest of the week, and I will send the rest of it to you by Friday. Now, go and pack!" She stood firmly in font of him, and stared at him right in the eyes, as if daring him to disobey her. _

"_You're actually serious?!" Her face didn't move, she just continued to stand and stare in front of him "Alright, but before I do could you at least tell me what prompted this little plan of yours. I mean is not as if I've been behaving any differently to how I normally am, I mean I've just been acting the same way I always do. It's never seemed to bother you before. No wait! Let me guess. You've got a new boyfriend who's all into religion, and he's trying to 'save' you from all the evils and wrongdoings in your life! Me included, right? So, what is he a Methodist?"_

"_Jess-"_

"_Baptist? Evangelist? Muslim? –"_

"_Jess, that's not what-"_

"_No, I know, he's a Harry Krishna! Of course, I mean all you've ever wanted to do was wear a Moo Moo, and play the tambourine all day! He sounds perfect for you. Well, don't mind me I have some packing to do; I don't wanna be in your way!"_

"_Jess, THERE'S NO GUY!"_

"_Huh, well I guess there really is a first time for everything!" _

"_I'm going to choose to ignore that last remark, because I know you're upset."_

"_Have you been reading those parenting books again? You know, you'd be surprised at how many parents choose to read them before they screw their kid up, not when the damage is done and he's fully grown!"_

"_Just because you shave and have sex with half the girls in the neighbourhood, does not mean you're fully grown!"_

"_Well, I guess sleeping around is something you'd know all about isn't it?!" SMACK! Liz slapped him hard across the cheek, leaving a red mark that would be there for hours._

"_Oh, god, Jess, I'm sorry." She moved to hug him but he moved away. "Look, this is exactly why you have to go and live with your uncle. We both need to sort ourselves out; we will kill each other if we stay together much longer. Jess, if you stay here you will end up dead in a ditch or in prison before your next birthday. Honestly, the way you live your life it's a wonder something like that hasn't happened already. You drink, smoke, you stay out all night without feeling the need to call, you cut school, steal, you're constantly being brought home by the cops-"_

"_Well, I guess my mommy should have taught me better!"_

"_Oh, and lets talk about all the naked girls I find in your room, for just a second, shall we?" she continued, ignoring him. "How many different girls have I caught you with this month alone?! Do you even know the names of half of them? Are you being safe? Do you really want a repeat of last year, with Connie and Jac-"_

"_DON'T YOU DARE BRING THEM INTO THIS! THEY WOULD STILL BE HERE RIGHT NOW IF IT WASN'T FOR YOU!"_

"_THE ONLY THING THAT I AM GUILTY OF IN THAT SITUATION WAS TRYING TO PRESERVE JUST SOME OF YOUR CHILDHOOD JESS! YOU WEREN'T READY!"_

"_IT WASN'T YOUR CHOICE!"_

"_YES IT WAS! I'M YOUR MOTHER!"_

"_REALLY, WELL YOU GOT SOME FUNNY WAYS OF SHOWING IT, LADY! You know what forget it, I am gonna leave! I'll only have to stay there until I graduate, right. Then I can go wherever the hell I want and with any luck I won't have to see you ever again!" He then stormed across the apartment and went into his room, slamming the door shut behind him. Forty five minutes later he was on a bus and heading to Stars Hollow._

_End Flashback_

Enough! He shook his head and brought himself out of the memory. He really didn't want to relive it. God, it had been an awful day. Well, with the exception of one small part. For a brief moment, his rarely ever seen but truly charismatic, crooked smile crept across his face. That short-lived scene after his shower today, was constantly replaying in the back of his mind. If he didn't keep his dreams under control he was going to need another cold shower. Uugghh, he moaned. How was he going to cope living in this house, when he couldn't get his step-cousin's, (if there was such a thing), breasts out of his mind. In the few seconds which Lorelai and Luke had stopped berating him with questions, he had taken the time to observe Rory. She seemed very timid but he suspected from the way she had yelled at him earlier, she was in fact really sexy and firm when she got all riled up. She was perhaps very sheltered, and coddled to a certain extent, as if she was some kind of china doll that would shatter at the slightest touch. But he could already see that there was a fire in her that was aching to get out. Maybe he would be the one to help her. He shook his head again at the thought. Luke's step-daughter, he reminded himself. Yes, but not his actual daughter, a slightly more wily and horny part of him remembered.

He took one last, long drag from his cigarette, and then flicked across towards the bushes. There, he thought, Litter. It will rock their tiny little worlds! He got up and stretched out his arms behind his back, then let out a big yawn. It had been a long day. Maybe getting some sleep wasn't such a bad idea. He turned around and opened the back door and then stepped back into the kitchen. He began to make hi way back to the living room, when a voice sounded, behind him. "Smoking can kill you, yah know!" He whipped round, and saw Rory stood next to the fridge with a glass of milk in her hands.

Rory had been lying awake for hours, just listening to the silence. That night, she had tried reading, doing extra credit assignments, cleaning her room, even organising her sock draw by colour – anything to stop her from leaving her room and running into their new permanent house guest. He'd seen her topless! When they met, she had been topless! And he had just been wearing a towel! A towel was the only thing that had been covering his wet, glistening toned ches- OH GOD! She had to stop thinking about it! She had to make a decision about Dean before adding yet more boy trouble to the mix. Oh, Dean. Sweet, reliable Dean. It was hard. She really cared about him. She did. Her past actions may not have proved that but she did. But she wasn't in love with him. And she knew that ultimately she didn't really want to be with him and he deserved somebody that did. It was just hard thinking of a way to do it. She'd never broken up with someone before. And she really didn't want to hurt him. Oh it was all giving her a headache.

She decided a glass of milk might help her sleep, so she got up out of bed and went into the kitchen. As she moved towards the fridge, the back door opened and she jumped back in fright; grabbing the closest thing to her, for protection. As soon as she raised her arms in front of hr Jess sauntered in, smirking.

"Are you crazy!" she hissed, not wanting to wake her Mom and Luke. "What the hell are you doing?!

"I didn't think your Mom would appreciate me smoking inside! What are you doing up?"

"I couldn't sleep so I came to get some milk, and then I thought some crazed lunatic was breaking in to my house!" Jess couldn't help but laugh at this.

"Look, from what I've seen today this town has plenty of lunatics, but I don't think that any of them are dangerous. And if they are you should probably think about locking your back door. Also, if I was a house robbing lunatic, what would you have done? '_Loafed_' me to death?" It was then she realised, that instead of picking up a rolling pin or a knife, she was holding half of a French baguette that was left over from dinner. She blushed, embarrassed by her choice of weapon.

"Smoking can kill you, you know!"

"Thanks for the information. Look I know things were a little awkward after our semi-naked run in this afternoon but I promise I won't mention it, again, to anyone." He smiled, trying to make her more comfortable. He had a beautiful smile. A beautiful crooked smile which reached up to his gorgeous brown eyes, making them shine ever so brightly in the dim light of the kitchen. "How about we start over? Hello, my name is Jess Mariano. I'm seventeen years old and from New York. My favourite colour is black to match my soul. I like rock and punk but I can't stand rap. And my pot head mother just sent me to live with complete strangers in a really weird town." She laughed, and shook his hand as he held it out.

"Hello, my name is Lorelai Leigh Gilmore, but everyone calls me Rory. I'm from this crazy town, Stars Hollow. I don't really have a favourite colour but if I did it probably would blue."

"That's diplomatic."

"Yeah, and I love to read, I like rock and punk but can't stand rap. My Mom had me when she was sixteen and is now married to Luke. Me and my mom are complete coffee and junk food addicts. Oh, and I go to Private school."

"Well, it's very nice to meet you Rory."

"It's nice to meet you too, Jess. I'm gonna go back to bed now."

"What about your drink?"

"I'm suddenly not thirsty, anymore. Goodnight."

"Goodnight. Oh, and Rory-"

"Yeah?"

"Nice _rack _by the way!" Her face flashed with horror and she ran back to her room and slammed the door shut behind her. He chuckled, beside himself. Maybe this place really wouldn't be so bad.

**Please let me know what you think!**


	3. Boyfriend Culling

**Crooked Smile**

**Chapter 3 – Boyfriend Culling**

The rest of the weekend went by uneventful: particularly as Rory was avoiding Jess at all costs. It was time for Jess to start is ascent into the pubescent oblivion known as High school. It wasn't as though Jess struggled with the work; in fact most of it was too easy. That was the main problem. It bored him. He was never going to be able to afford college, and with his permanent record no school in their right mind would accept him. So, he just couldn't see the point in wasting his time. But to Luke it seemed like a pretty big deal. He might as well give it a go. He finished getting dressed and went downstairs for breakfast. At least that smelt nice; the only upside to this sure to be nauseating day.

As he descended the staircase, Rory entered the living room, dressed in her Chilton uniform. He stopped, stunned.

"Whoa." Rory looked up surprised at his presence.

"What?" she asked, still slightly uncomfortable, after avoiding him all weekend. "Are you okay?"

"What? Oh, yeah, err, just a little dizzy, I didn't get much sleep last night." God, she wore_ that _everyday. He briefly remembered her mentioning that she went to private school, but for some reason he hadn't made the connection between that and girl in really hot outfit!

He was still standing on the staircase when she bent down to put some books in her bag, he then snapped back into life and went to the kitchen for some breakfast before he needed to take yet, another, cold shower.

Thirty minutes later, he was out of the house, heading to school with his uncle Luke by his side.

"You don't have to walk me to school, yah no, I'm not nine."

"Look, you have to meet the principle today and a parent or guardian has to be there with you so you can enrol."

"Well, I guess asking a parent to be there is just that bit too much, right?"

"Look, Jess, you know your mom thinks that you being here is what's best for you. I know she can be pretty flaky at times, but you know that she does her best. Come on," he said as they entered a large, well kept, red brick building, "the principles' office is this way." And they headed, straight down the main hallway. Jess remained silent, mulling over what Luke had said about his mom and her always trying her best. Well, if what she's been doing for the past seventeen years is her best then he was as sure as hell glad to get away from her before she started doing her worst.

When they finally got to the Principle's office, he began to take in his surroundings. It was still rather early, so there were very few other students around. But those that were there, seemed to find him oddly curious. Every single one of them was staring at him. God, have they never had a new student here before? He turned away from them and followed Luke inside the office. Once they were inside a ninety-year-old secretary met them, and then they were told to sit and wait until the principle was ready to see them. They sat in silence for about five minutes until Luke could take it no more.

"This place isn't really so bad, once you get used to it."

"Huh."

"Yep." Like sighed, he could already see that Jess was not going to make this easy. Just then a red bulb on Mrs Wheeler's desk lit up.

"Mr Merton, will see you now." With that they got up and went to see the principle. When they entered Jess was faced with a middle aged black man, with glasses and a moustache, looking at them severely over the top of and open folder.

"Hello Mr Danes, and Jess – I believe?" Jess nodded quickly, eager to get this meeting over with. "Well please sit down won't you? Now Jess, I've read your transcripts that your school in New York sent over. I have to tell you that it took me practically the whole weekend to get through it. It appears as if you were quite a notorious figure at your last school, Mr Mariano." Jess said nothing, but he could feel Luke's eyes continuously flickering towards him, and it made him shift uncomfortably in his seat. "Now, from what I've gathered your home life hasn't exactly been the most stable, but hopefully that's about to change. I will impress it upon you to take advantage of your new situation and make a fresh start. Perhaps finally live up to your potential. But I must warn you; I will not tolerate any shenanigans, from you or anyone else at Stars Hollow High. Is that understood?"

"Yes." Jess muttered grudgingly.

"Yes, Mr-?"

"Yes. Mr MURTON."

"Very good. Well, if you go and see Miss Aubrey at the front desk, she will give you your class timetable and a map of the school, along with the school code of conduct. I suggest you memorize that Jess, we don't want you getting in to trouble now, do we?" Jess for the urge to snort. Get in trouble? Did this bozo really read that file? "Good day to you both."

-Later at the end of the school day back at the crap shack. -

Thank god this day was over, Jess groaned as he crashed out on his bed. He'd been leered at, ogled, threatened and hit on. Not that he really minded the last part, but most of these girls didn't seem to have five brain cells between them, he could only spend so much time pretending to be interested in what Muffin or Cissy did in gym class, in the hopes of it leading to sex. Maybe later in the week: when he wasn't so pissed off at the world around. Actually, better make that the end of the month.

Argh, he couldn't stand being cooped up in his room one more day. He decided to go for a walk, and clear his head before Luke and Lorelai came home and started bombarding him with questions again. He wondered for about twenty minutes, until he came across and old, rickety plank bridge, not far from the high school. But as everyone had already gone home, it was now quiet and peaceful. He sat down and took in his surroundings. It was a smallish lake, surrounded by trees and with the odd duck and swan floating by. In a way it reminded him of some of the parks in New York, without the sounds of police cars zooming by. He had to admit, peace and quiet was something rarely found in New York.

He sighed and pulled out his pack of cigarettes, lighting what was probably his tenth one of the day. Smoking them was about all that kept him from punching out one of the kids from his new school today. God! What a bunch of freaks! He really couldn't get over this place. Every single desk was pristine, nobody cut in line in the cafeteria, and they all followed the dress code to a tee and said the pledge of allegiance in six different languages. Two of which he'd never heard of before.

He shook his head and took another drag of his cigarette, allowing his mind to wander. Finally, his mind landed on Rory, once again. (And that wonderful little uniform of hers.) He never met anyone quite like her before, someone so smart and beautiful. Her eyes were a blue like he'd never seen, and her smile was so sweet and innocent, and she blushed so easily, and her breasts – well you know what he thought of her breasts. But, ultimately, he knew thinking about her and wanting her couldn't come to anything: at least not anything good.

Rory was the type of girl that needed to be treated like a princess, something that he knew he really wasn't capable of. Jess's past relationships read more like notch after notch on his bedpost. A string of one-night stands and the occasional weeklong flings. The closest he had ever had to a girlfriend was Connie. And there he was stretching the term to its limit. Connie, god where was she now? Was she okay? Was Jacob still with her? No! No, no, no! He wasn't going to allow himself to think about them. He couldn't think about them? It hurt too much.

Rory got off of the bus, home from a day's toil at Chilton. The work hadn't been the problem, not even Paris. It was because that today, right now in fact, was the time to break things off with Dean. Dean was, in most respects a great boyfriend, if a little too possessive at times. He just wasn't the right boy for her. She new that, and it was time that he knew that they had no future. She had to break it off before things got too out of control.

She had tried to think of how to go about it for days. What she needed to say. How could she not to hurt his feelings too much? But whenever she tried to focus, her mind would stray and begin to linger on her new housemate. He truly was a mysterious one. She new she shouldn't think about it but every now and then, his wet glistening chest would creep into her thoughts. There was no denying it. And a tiny part of her couldn't help but want to be free of Dean so that she could fool around with Jess. WAIT! NO! NO! NO! She didn't mean that! And quickly tried to shake that thought from her mind. She wasn't a _fool around _kind of girl.

'But that's what you did with Tristan –when you were still with Dean!' said a little voice inside her head. She shuddered at the thought. Nobody needed to know about that. She'd just let her hormones take over for a short while. She simply lost her head for a bit.

'Yeah, and you hope to lose more than that with Jess living with you! – STOP IT!' she told herself again. But she barely had the time to reprimand herself as she saw Dean fast approaching her. She needed to focus on the task at hand. It was now or never.

Jess finally decided that it was time to head home. The rumbling of his stomach reminded him of how he hadn't eaten anything since breakfast. Stars Hollow High cuisine wasn't quite up to his standards; and his were pretty low. He was sure he had seen something similar being served up in an old prison movie – either that or some dumpster in New York. Whichever it was, he hadn't been brave enough to try it.

.

As he came onto the main street, he spotted Rory. She was sitting on the bench next to the bus stop. He was trying to decide whether or not to go over and speak to her. But before he had made up his mind, some floppy haired giant came over to her, and kissed her on the lips. Huh. He didn't know she had a boyfriend. Couldn't she do better than that! He looked like Dracula's nephew. Maybe he had best talk to her later.

Lorelai and Luke both came home around seven, but Rory still wasn't home. He soon discovered that this was very odd. "Jess, has Rory been home yet today?" she asked him, as he was laid on the sofa, watching television.

"Not that I know of."

"She hasn't been home at all? Oh, God what if she missed her bus, and there wasn't another one. She may not have cell coverage – OH GOD, she might have had to go to my mother's house, if she was stuck there!"

"Lorelai calm down!" said Luke, desperately trying to calm down his wife. "She's been late home before. She could have gone to see Lane or Dean and just lost track of time." Dean? The boys suddenly made Jess's ears perk up. Dean was that the guy she was with earlier. Desperate for more information, he suddenly decided to speak up.

"Well, she definitely didn't miss her bus. I saw her at the bus stop when I was walking through town, she was talking to some tall, floppy haired guy." Lorelai suddenly breathed a sigh of relief.

"Oh good, she's with Dean. Well, I'll give her ten more minutes before I call her." As she said this, there was the sound of fumbling keys opening the front door. It then opened, and a rather distressed looking Rory stepped inside.

Rory sat in the same spot for almost four hours. She'd done it. Her first relationship was finally over. It was strange really; she thought that she would feel this overpowering sense of guilt. And she did feel guilty for leading him so long, but that was nothing to sheer sensation of relief. He had been upset at first but she could tell that he had been expecting it for sometime. It hadn't taken very long, twenty minutes at the most, yet she was still sat in the same spot. She couldn't move. Her mind was reeling. What was she supposed to do now? A part of her felt as if she should be jumping for joy but another part felt as if she should be sobbing. Unable to decide, she just sat there. She watched as passers by carried out their daily lives. Picking kids up from school, coming home from work, shopping, and getting dinner; never before had the quaint small town she loved so dearly felt so busy before. And then suddenly she could move.

It was dark before she got home, she couldn't believe just how long she had been sat at the bus stop, and she wasn't sure how to explain where she had been. She reached the porch braced her self and stepped in.

"RORY! Oh, good, thank god your home." Cried Lorelai and instantly grabbed her and pulled her tightly into her arms. Luke signalled to Jess to move into the Kitchen and allow the two to talk alone. Jess got the impression that it was a good thing to be out of the way when a barney between the Gilmore Girls occurs. Otherwise there may be casualties.

"Can't breath Mom."

"Oh, sorry. Right now you can breath would you please explain to me where you were until this hour? I've been worried sick!"

"This hour? Mom, it's barely past seven and this is Stars Hollow. The most dangerous thing that could happen is coming across Kirk in a mime outfit!"

"Mime outfit?"

"Or something equally weird! Look Mom, I'm tired I just wanna go to bed."

"I thought you just said it was barely past seven."

"Yah, well it's been a long rotten day."

"Luke made dinner."

"I'll warm it up later."

"Hey listen, crabby lady, Luke's lasagne cures everything; there even considering giving him a Nobel Prize and a Michelin Star rolled in one. A bunch of science geeks and snooty French chiefs are practically lining up outside the door to worship him." desperately trying to lighten the mood.

"MOM! I know you live in your own semi-detached world half the time but a lump of lasagne and witty banter does not cure everything! You don't know what sort of a day I have had!"

"Ok." Lorelai suddenly became very cautious, knowing it was better to tread lightly when her daughter was in such a mood. She was too much like herself in that respect. "Tell me what sort of a day you've had!"

"Oh, so now you wanna talk to me? For these past few month it's been almost as if I haven't existed!"

"That is not true!"

"Yes it is! And I don't know why it is, but that how things are now! You have a new life and I don't fit."

"Of course you fit! You're the centre piece, the main event, what everything is essentially built around!"

"Well, I don't feel that right now."

"Well, honey talk to me. You've been so distant lately I just thought you needed your space. Tell me how do you feel?"

"Right now, I feel tired."

"Well, okay go to bed but we'll talk in the morning."

"Fine. Night,"

"Night, honey," and she turned back to the living room, not wanting to bother her daughter further.

Later in the evening, Jess still remained on the couch pretending to read, even after Luke and Lorelai had gone up. Instead of heading up to his room, as soon as he was free after dinner, he waited silently for Rory to once again exit her room. He was convinced she would have to come out of her room sooner or later, she hadn't eaten anything all evening and from what he'd seen, the Gilmore girls didn't do too well unless they ate every hour or so. Also, he was curious. So curious he was almost embarrassed to admit it to himself; it was almost as if he was a thirteen year old with a crush. He wanted to know where she was tonight, whom that guy was that she had been with at the bus stop, and why she had consisted to lock herself in her room when she finally came home?

He looked at the clock, 11:45. He sighed there was no way that she was going to come out now, he should probably go to bed; especially if he had to face the glories of Stars Hollow high the next morning. He stood up and threw his book onto the coffee table. He then walked into the kitchen for a glass of water, as he reached the cupboard, he heard the creak of a door behind him and whipped around. There stood Rory.

Rory and Jess were somehow, once again, alone, in the kitchen in the middle of the night. She was still half dressed in her Chilton uniform, after simply passing out on her bed as soon as she got home. She tried desperately to forget the events that had passed throughout the awful day. Her sleep had been unsuccessful in that respect; Jess wasn't. He appeared before her, bare-chested and simply glowing in the moonlight. God, he was beautiful. She was unable to stop her eyes from roaming all over his body: it was dark, so he couldn't see her blush.

Unbeknownst to Rory, Jess was having a similar problem; there was just something about her in THAT uniform! He wished he wasn't such a guy at times, but everybody had his or her own fantasies, right? Her hair was a mess, and her shirt was un-tucked and crumpled, and her legs and feet were bare from discarding her navy tights earlier in the evening. Everything about the way she looked was challenging him to touch her. It was this thought that finally shook him back into reality, and ended the age long silence.

"Hey. So, you're up!"

"Err, yeah. I'm sorry, if I acted a little weird I just had a pretty rough day." She shifted uncomfortably on the spot.

"Err, are you hungry?" Rory smiled.

"A little, I haven't really eaten all day."

"Really? Wow, you really have had a rough day!"

"What?"

"Well, nothing, it's just I've been hear long enough to realise that you Gilmore Girls don't really do well when your hungry. Did you contemplate that if you'd eaten your day would have gone better?"

"Huh, very astute observation. And as much as I wanted to eat, I just felt a little sick and it put me off."

"You're not pregnant are you?"

"WHAT? NO!"

"Sorry, it's common question at my previous school; particularly when a girl says she been being sick."

"Yeah, well, trust me, I'm not pregnant. If I was I could start a new religion."

"Ah." He nodded. So she was a virgin. It's not that he found that fact so surprising, but when he saw that guy mauling her at the bus stop, he began to have doubts. "So, what do you want to eat?"

"Err, I think I'll just have some coffee. I can get it."

"K," he watched her as she moved towards the cupboard to get herself a mug, and how her delicate cream thighs were revealed as she stretched out to reach one down. The back of her shirt was crumpled and her hair was a mess. It was clear that she'd been having a rough night's sleep. "So, rough day, huh?"

"Erm, you could say that."

"Do you mind if I ask what-"

"I broke up with my boyfriend of over a year."

"That guy you were with at the bus stop?" Rory looked up at him stunned.

"You were watching us?"

"Well, I couldn't really help it. The last time I saw something like that it was on the nature channel. I thought he was trying to eat you at one point."

"Do you get off on trying to be a rude pompous jackass, or does it just come naturally to you?"

"Naturally. But seriously, you didn't really look as if you were about to break up."

"Yeah, well he sort of grabbed me before I could- why am I telling you this?"

"Beats me I'm not encouraging it?" He smirked at her as she moved to pour her coffee. "Anyway, it's over."

"Why?"

"Are you always this nosey?"

"Well, I'm living in a small town now, so I figure I'll need to know some of the gossip to fit in." He smirked at her again. "But seriously you don't have to tell me if you don't want to." Rory was silent for a minute. She could delve in to the usual lines of "He was such a great guy but I just want to be alone right now," or "We'd really just grown apart." Instead she decided to opt for the plain and simple truth.

"I was bored."

"Bored?"

"Yes. That's all. We'd been together for over a year and now I'm bored, so I dumped him."

"Well, that sounds-"

"Bitchy?"

"No. Reasonable. You're seventeen why be stuck with someone that you don't really enjoy being with? You shouldn't be doing that until you're a single mother in your thirties, who's been married and divorced more times than Elizabeth Taylor and never held down a half-decent job for longer than eight months." Rory stared at him for a minute.

"Well, that's quite a vision for my life you've got there. We've known each other, for what, a week now? My company hasn't been all that bad has it?"

"I must be deflecting. It's what I've been living with for the past seventeen years. Except she hasn't always been in her thirties." Rory stood their silently for a minute, not entirly sure of what she should say. "Don't worry, she often left me speechless too." Rory nodded.

"Well, I think I'm just gonna go back to bed. I have a Latin test tomorrow."

"Latin? Now, there's something you'll use all the time." She chuckled at him. He really was very different.

"Goodnight Jess." And she turned back to her room.

"Hey, Rory."

"If this is another perverted comment, I would much rather you keep it to yourself." She replied quickly, remembering the previous night.

"Not perverted. Not yet anyway." He smirked, and she turned away again. "I just wanted to say, that I'm really glad that you don't have a boyfriend. It'll make my dreams tonight much less awkward."


End file.
